Dear Prudence,One of my closest friends in high school recently organized our 10-year reunion. I wasn’t able to attend, but the night of the event, he sent me a text saying, “We all miss you.” That was immediately followed by an extremely crude request for me to describe features of my genitals. I was shocked and upset. A friend says he was probably drunk and I should laugh it off. I’m not ready to, and I don’t think being drunk is an excuse. He had a chance to back off but persisted, even after I texted back “WTF?” He also hasn’t apologized in the days since. I feel that we don’t have a rapport where he could ask me that out of the blue, especially since we’ve drifted apart in the last decade. And I don’t feel that the fact we are both men makes it OK—I feel harassed and demeaned. I can’t let it go. Should I confront him about it or just continue to let our friendship fall by the wayside naturally?—Old Friend Crossed New Line

Getting drunk isn’t a free pass to ask old friends about their genitals. It’s a bizarre, jarring follow-up to “We all miss you,” and the fact that he kept pushing even after you responded in surprise and alarm is frankly cruel. I get that people who are very close to one another may have different rules of engagement when it comes to personal questions or jokes, but even if you two had remained close and had a history of joking with each other, it would still be fine for you to say “This isn’t funny and I don’t like it” and expect your friend to knock it off. It’s entirely up to you whether you’d like to tell this guy just how out of line he was or if you’d prefer simply to block his number and move on with your life. Since it’s still on your mind days later and you don’t feel like you can let it go, I think you might benefit from saying something to him and asking for an apology. That doesn’t mean you have to become good friends again—you may just want the apology and to move on with your life—but you don’t have to laugh it off, make excuses for his drunkenness, or otherwise “get over it.”

Dear Prudence, When she was 24, my girlfriend, “Lisa,” lost her mother to a sudden illness. By all accounts, Lisa’s mother was incredible—intelligent, accomplished, a pillar of the community. Five years later, Lisa still struggles with the loss. I know I will never truly understand what this feels like, as my own mother is alive and well, but I’ve tried to be supportive nevertheless. Lisa has been pretty clear that she has “little patience” for people who have bad relationships with their (living) mothers. My own mother was borderline abusive. She kicked me out for my sexual orientation, turned my siblings against one another, and cheated on my father for years. We do not have a good relationship. Lisa knows to not push me to make amends. However, she is impatient and displeased that I don’t “appreciate” my mother while she’s still alive. This is the only fight Lisa and I keep coming back to. In all other ways, we are compatible, and she’s the love of my life. But I will never be close with my mother, and Lisa’s will never come back. Does this mean we will never get over this dynamic? Or should we just agree to put a moratorium on all mother-related discussions? What if this keeps coming up? —Maternal Woes

Since Lisa’s your girlfriend and not just a buddy you grab drinks with after work, it’ll be difficult to never discuss your mother with her again. To whatever extent it’s possible, however, limiting the amount of time you spend discussing your mother with her will go a long way toward keeping the peace. That’s best as a short-term strategy. If Lisa’s really the love of your life and you can see yourself staying together for years, you two are going to have to find a way to at least occasionally talk about your problems with your mother that don’t all come back to “Your mother’s still alive, so I don’t really want to hear about your issues with her.”

The important distinction between Lisa’s situation and yours, though, is that she had a mother who was capableof intimacy without causing harm. You say Lisa knows not to push you to make amends, but I’m not sure what amends you could offer your mother, given that the problems in your relationship stem from her rejection of your sexual orientation—you can’t, and shouldn’t, apologize for that. Any repair would have to come from your mother’s own admission of how she harmed you, and as long as she’s unable or unwilling to do that, there’s a limit to how close you could ever be with her without hurting yourself. The maternal relationship is not a transferable one. Whether or not you speak to your mother can neither enhance nor discredit Lisa’s relationship with hers. You can give her space to grieve, let her tell you what her mother was like, try to honor her memory together. And for her part, Lisa should not pressure you to get closer with your mother for the mere sake of maternal proximity, without regard for your own history or well-being.

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Dear Prudence, Ten years ago, fresh out of college, I worked for the most horrible human being I’ve ever met. “Carlotta” verbally and emotionally abused me and other employees. She’s incredibly good at her job but vicious as a boss. I’m still not certain whether the toll of the two years I worked for her are worth what it did for my career. I lost so much weight I stopped menstruating, and I only quit when my hair started falling out. Carlotta is wealthy and vindictive. I’ve never spoken about her to anyone other than my therapist and my husband for fear she’d wreak havoc on my career or sue me. Now a family friend’s daughter is graduating and entering the same field as me. She emailed me last week, ecstatic because she’s got an interview with Carlotta. We’ll be seeing each other at several Christmas gatherings, and she wants to take me out for coffee to discuss my experience there. I’m ashamed to admit that my sense of self-preservation has caused me to remain mum. I don’t know what to do or say to her other than the truth: Run, run far away from this woman! If the daughter repeats what I’ve said, there could be repercussions for my career. If I say nothing and she gets the job, I’ve set her up for a torturous experience. What should I do? —Bad Boss Ghost

I’ll take your word for it that Carlotta has both the ability and the motive to seek to damage your career, but I don’t think you have to worry too much about a potential lawsuit as long as you’re careful about how you describe your time there, sticking only to what was difficult for you and avoiding making claims about whether she’s the spawn of Satan. It may ease your mind to talk to a lawyer to learn more about on just what grounds Carlotta could potentially initiate a lawsuit. But it’s been almost a decade since you last worked for Carlotta, you’ve had time to build up an independent body of work, and you are in a position to help someone young and relatively inexperienced. That doesn’t mean you have to share every detail of your time there or feel responsible for whether she takes the job, but try to give her an accurate sense of what she can expect if she does. You can also tell her that you’re sharing this information confidentially and that you’d appreciate it if she didn’t share it with anyone. “I found I was effectively on call 24/7, and the stress was very difficult for me. If I had it to do over again, I’d have gotten my start at another office” is not inflammatory in the same way that “Carlotta tried to ruin my life, and she’ll ruin yours too” might be, while still making it perfectly clear that you think she should pass on this opportunity.

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Dear Prudence, I recently found out a family friend has an illness that will probably kill her soon. We aren’t very close, but I want to reach out in some way. If we were closer or she lived nearby, I’d offer to help out, but that’s not really possible. It would really just be a note to offer sympathy. I’m not sure how to phrase this tactfully, when it’s clear I’m only getting in touch to say, in effect, “Sorry you’re dying.” But I can imagine it would be terrible to be sick, lonely, or afraid and have people vanish just because it’s awkward or painful to address it directly. Is there some way of framing this that offers kindness without beating someone over the head with their own diagnosis? —Terminal Etiquette

I think this warrants a phone call! You can also send a note of sympathy—something along the lines of “I’m so sorry to hear about your diagnosis. I’m thinking of you often. I wish I lived closer to you so I could offer more practical help, but if there’s anything I can do to help, please call on me, even if you just need someone to talk to.” But call first so that you can tell her you care about her and you’re so sorry about her illness in real time. You might also ask if she would care for flowers, or to have a meal delivered to her house, or for some other little gift she might appreciate. It’s always good to check before sending anything, because she might be currently inundated with flowers or have more casseroles in her freezer than she knows what to do with, and the last thing you want is to inconvenience her while she’s dying. But a phone call to check in will be a great way to get a read on what, if anything, she’d like from you, and a card to follow will help concretize your offer of support.

Dear Prudence Uncensored

“I hope that if I heard something like this from someone that I would not take a job!”

Dear Prudence,For five years, I was a stepmother in all but name (we never married) to two little girls. I stayed in the relationship for them longer than I would have otherwise. Their father, while charming, had a gambling addiction and constantly cheated on me. I left when the oldest girl was 9. I tried to keep in touch, but their father was vindictive and cut off all contact. I couldn’t even say goodbye over the phone. He found someone else in less than four months and married her. That was four years ago. I have since moved out of state and recently moved back. Through social media, I learned my ex killed himself, leaving his widow with five children. She isn’t doing well financially and has created several crowdfunding posts. I am doing quite well: a new promotion, a new house, and a new car. I have the means to help her. Part of me dreams of taking the girls in, but I know that is unrealistic. I do not know the girls’ legal situation, whether their stepmother adopted them. Their father had no living family, save a senile great-aunt. My concern is the girls. I don’t want to offer financial help and have it squandered on other matters (their father once gambled away the money I gave him to pay for their prescriptions). What should I do?—Afraid to Help

If the children have no other relatives on their father’s side, and it sounds like their biological mother is either unreachable or also deceased, then it’s likely their stepmother has the strongest (if not only) claim to custody. While I don’t think you should assume that she’s as likely to misuse any money you give her in the same way your ex might have, I can appreciate that you want to make sure you’re helping the girls you once helped raise, as well as the other vulnerable children in the house. But I don’t think you can offer to help just some of this woman’s children and not the others, and you also can’t show up after four years’ absence (for which you’re not responsible, of course) and ask to take in just two of them. Have you considered getting in touch with your ex’s widow and offering to help with occasional child care? I’m sure she could use practical as well as financial help, and she might be open to letting you visit the girls, where your ex wasn’t. You can start small by trying to re-establish a line of contact before offering more substantive financial support. If she’s not open to it, then you’ll have to ask yourself whether you’re willing to risk the possibility of some of your offering being spent on nonessentials before giving. Given your love for the girls and the genuinely difficult nature of their position, I think you can safely assume that the whole family needs the money and that it’ll go toward keeping a roof over their heads. In my view, it’d be worth the risk.

Dear Prudence, A decade ago, we extended a personal loan of over $10,000 to my father-in-law’s business. Instead, his daughter and her husband used it to take expensive personal trips, buy jewelry, and gamble. When the accountant came forward, it broke our family in half. My father-in-law ended up having a medical relapse and going into the hospital. We gave my sister-in-law a chance to repay the money rather than press charges. She and her husband refused. We took matters to the police. They ended up plea-bargaining down but showed no remorse, left town, and didn’t even bother to come back for my father-in-law’s funeral (but did have their lawyer call about the will—nothing was left to them, but there was an educational trust for all the grandchildren).

Their daughters were young when this happened; they are adults now. Neither of the girls has come forward to claim her portion of the trust, despite our lawyer sending official mail. I was able to find both of them easily on social media. I am torn—should I reach out and contact them personally? What should I say? What if they ask me about the estrangement? —Long-Ago Grift

I think you should! If the official mail was sent to, say, their parents’ address, there’s a real chance the girls never saw it and don’t know they’ve inherited money they could use toward their education. (Or, like a lot of people who grew up after email became the most common form of communication, they may not be in the habit of opening their physical mail regularly. I am not attempting to make generalizations about all young people, but it’s possible!) Send a brief note explaining who you are and that you wanted to make sure they knew about their inheritance since they never responded to their official notifications. You can even give them the lawyer’s contact information if you’re worried their parents might have misrepresented you to them and might be suspicious on first hearing from you. If they ask you about the nature of the estrangement, you can be both honest and brief: “We loaned your parents money for our father-in-law’s business, and they spent it elsewhere. It was a difficult time.” Then get back to focusing on the reason for your getting in touch. But if all you want to do is provide them with the lawyer’s name and contact information, you can absolutely do so without going into details or answering questions about their parents’ betrayal.